Synthesis of Calix[4]arene Appended Lactosylated G1 and Galacto­sylated G2 Generation Glycodendrimers using a ‘CuAAC’ Click Approach

Sunil Kumar; Mangal S. Yadav; Sumit K. Singh; Sanchayita Rajkhowa; Vinod K. Tiwari

doi:10.1055/a-2063-4139

SynOpen, Inhaltsverzeichnis

CC BY 4.0 · SynOpen 2023; 07(02): 145-153
DOI: 10.1055/a-2063-4139

paper

Virtual Collection Click Chemistry and Drug Discovery

Synthesis of Calix[4]arene Appended Lactosylated G₁ and Galactosylated G₂ Generation Glycodendrimers using a ‘CuAAC’ Click Approach

Autor*innen

Sunil Kumar

^aDepartment of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India
Mangal S. Yadav

^aDepartment of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India
Sumit K. Singh

^aDepartment of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India
Sanchayita Rajkhowa

^bDepartment of Chemistry, The Royal Global University, Guwahati-781035, Assam, INDIA
Vinod K. Tiwari ∗

^aDepartment of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India

Abstract

Alle Artikel dieser Rubrik

This manuscript is dedicated to (Late) Prof. Alan R. Katritzky for his contributions to benzotriazole chemistry.

Abstract

A modular and highly reliable click approach is applied for the expeditious synthesis of lactose- and galactose-coated calixarene-cored G₁ and G₂ generation glycodendrimers, respectively. The developed calixarene glycodendrimers have been characterized by using extensive spectral analysis including NMR (¹H and ¹³C), MS, IR, and SEC data.

Key words

azide - alkyne - click reaction - calix[4]arene - macrocyclic - glycodendrimer - catalysis

Volltext

Referenzen

References
1 Neri P, Sessler JL, Wang MX. Calixarenes and Beyond 2016

2a Nimse SB, Kim T. Chem. Soc. Rev. 2013; 42: 366
2b Dondoni A, Marra A. Chem. Rev. 2010; 110: 4949

3a Dondoni A, Marra A. J. Org. Chem. 2006; 71: 7546
3b Agrawal YK, Bhatt H. Bioinorg. Chem. Appl. 2004; 2: 237
3c Yousaf A, Hamid SA, Bunnori NM. Drug Des., Dev. Ther. 2015; 9: 2831

4a Tiwari VK, Mishra BB, Mishra KB, Mishra N, Singh AS, Chen X. Chem. Rev. 2016; 116: 3086
4b Agrahari AK, Singh AK, Singh AS, Singh M, Maji P, Yadav S, Rajkhowa S, Prakash P, Tiwari VK. New J. Chem. 2020; 44: 19300

5 Agrawal YK, Bhatt H. Bioinorg. Chem. Appl. 2004; 2: 237
6 Sgarlata C, Arena G, Longo E, Zhang D, Yang Y, Bartsch RA. J. Membr. Sci. 2008; 323: 444
7 Cabana N, Schulte E, Nunez JL, Quaino P. Chem. Phys. Lett. 2023; 811: 140210

8a Shinkai S, Araki K, Manabe O. J. Chem. Soc., Chem. Commun. 1988; 187
8b Sansone F, Dudic M, Donofrio G, Rivetti C, Baldini L, Casnati A, Cellai S, Ungaro R. J. Am. Chem. Soc. 2006; 128: 14528

9 Morales-Sanfrutos J, Ortega-Muñoz M, Lopez-Jaramillo J, Hernandez-Mateo F, Santoyo-Gonzalez F. J. Org. Chem. 2008; 73: 7768

10a Song M, Sun Z, Han C, Tian D, Li H, Kim JS. Chem. Asian J. 2014; 9: 2344
10b Sun Y, Mao X, Luo L, Tianand D, Li H. Org. Biomol. Chem. 2015; 13: 9294

11 Rodik V, Klymchenko AS, Jain N, Miroshnichenko SI, Richert L, Kalchenko VI, Mely Y. Chem. Eur. J. 2011; 17: 5526
12 Yoshida K, Fujii S, Takahashi R, Matsumoto S, Sakurai K. Langmuir 2017; 33: 9122
13 Pozar J, Cvetnic M, Usenik A, Cindro N, Horvat G, Leko K, Modrušan M, Tomišic V. Molecules 2022; 27: 470

14a Casnati A, Sansone F. Acc. Chem. Res. 2003; 36: 246
14b Miao F, Zhou J, Tian D, Li H. Org. Lett. 2012; 14: 3572

15a Cecioni S, Lalor R, Blanchard B, Praly J.-P, Imberty A, Matthews SE, Vidal S. Chem. Eur. J. 2009; 15: 13232
15b Kumar S, Yadav MS, Tiwari VK, Maddeshiya T, Pandey MD, Jaiswal MK. Org. Mat. 2023; DOI:

16a Agrahari AK, Jaiswal MK, Yadav MS, Tiwari VK. Carbohydr. Res. 2021; 508: 108403
16b Mendal M, Trnoe CW. Chem. Rev. 2008; 108: 2952
16c Agrahari AK, Kumar S, Pandey MD, Rajkhowa S, Jaiswal MK, Tiwari VK. ChemistrySelect 2022; 7: e202202273

17a Nayak M, Joshi DK, Kumar K, Singh AS, Tiwari VK, Bhattacharya S. Inorg. Chem. 2021; 60: 8075
17b Agrahari AK, Bose P, Jaiswal MK, Rajkhowa S, Singh AS, Hotha S, Mishra N, Tiwari VK. Chem. Rev. 2021; 121: 7638

18a Sareen N, Singh AS, Tiwari VK, Kant R, Bhattacharya S. Dalton Trans. 2017; 46: 12705
18b Baek MG, Roy R. Bioorg. Med. Chem. 2002; 10: 11

19a Mishra N, Singh AS, Agrahari AK, Singh SK, Singh M, Tiwari VK. ACS Comb. Sci. 2019; 21: 389
19b Mishra N, Singh SK, Singh AS, Agrahari AK, Tiwari VK. J. Org. Chem. 2021; 86: 17884
19c Singh SK, Kumar S, Yadav MS, Tiwari VK. J. Org. Chem. 2022; 87: 15389

20a Shen H, Shen C, Chen C, Wang A, Zhang P. Catal. Sci. Technol. 2015; 5: 2065
20b Singh SK, Mishra N, Kumar S, Jaiswal MK, Tiwari VK. ChemistrySelect 2022; 7: e202201314
20c Singh SK, Yadav MS, Singh AS, Agrahari AK, Mishra N, Kumar S, Tiwari VK. ACS Omega 2021; 6: 21125

21a Sharma R, Zhang I, Abbassi L, Rej R, Maysinger D, Roy R. Polym. Chem. 2015; 6: 1436
21b Camponovo J, Hadad C, Ruiz J, Cloutet E, Gatard S, Muzart J, Bouquillon S, Astruc D. J. Org. Chem. 2009; 74: 5071
21c Lee RT, Gabius H.-J, Lee YC. Carbohydr. Res. 1994; 254: 269

22a Bertozzi CR, Kiessling LL. Science 2001; 291: 2357
22b Tiwari VK. Carbohydrates in Drug Discovery and Development. Elsevier Inc; Amsterdam: 2020
22c Gabius HJ, Andre S, Barbero JJ, Romero A, Solis D. Trends Biochem. Sci. 2011; 36: 298
22d Lis H, Sharon N. Chem. Rev. 1998; 98, 637
22e Camponovo J, Hadad C, Ruiz J, Cloutet E, Gatard S, Muzart J. J. Org. Chem. 2009; 74: 5071
22f Mishra S, Upadhyay K, Mishra KB, Tripathi RP, Tiwari VK. Stud. Nat. Prod. Chem. 2016; 49: 307

23 Chabre YM, Roy R. Chem. Soc. Rev. 2013; 42: 4657
24 Marradi M, Cicchi S, Sansone F, Casnati A, Goti A. Beilstein J. Org. Chem. 2012; 8: 951
25 Pozar J, Cvetnic M, Usenik A, Cindro N, Horvat G, Leko K, Modrusan M, Tomisic V. Molecules 2022; 27: 470

26a Chabre YM, Brisebois PP, Abbassi L, Kerr SC, Fahy JV, Marcotte I, Roy R. J. Org. Chem. 2011; 76: 724
26b Imberty A, Chabre YM, Roy R. Chem. Eur. J. 2008; 14: 7490
26c Francand G, Kakkar A. Chem. Commun. 2008; 5267
26d Astruc D, Liang L, Rapakousiou A, Ruiz J. Acc. Chem. Res. 2012; 45: 630

27a Agrahari AK, Singh AS, Mukharjee RK, Tiwari VK. RSC Adv. 2020; 43: 31553
27b Agrahari AK, Kumar S, Sharma A, Tiwari VK. J. Chem. 2021; 4209514
27c Agrahari AK, Singh AS, Singh AK, Mishra N, Singh M, Prakas P, Tiwari VK. New J. Chem. 2019; 43: 12475

28a Kim JS, Quang DT. Chem. Rev. 2007; 107: 3780
28b Liu Z, He W, Guo Z. Chem. Soc. Rev. 2013; 42: 1568
28c Kim HJ, Lee MH, Mutihac L, Vicens J, Kim JS. Chem. Soc. Rev. 2012; 41: 1173

29 Tiwari VK. Chem. Rec. 2021; 21: 3029

Zusatzmaterial

Supporting Information (PDF) (opens in new window)

Synthesis of Calix[4]arene Appended Lactosylated G1 and Galacto­sylated G2 Generation Glycodendrimers using a ‘CuAAC’ Click Approach

Autor*innen

Synthesis of Calix[4]arene Appended Lactosylated G₁ and Galactosylated G₂ Generation Glycodendrimers using a ‘CuAAC’ Click Approach